Sean Parker
You just never know what to expect from films you see at film festivals. That may seem like a pretty obvious statement, but for those who’ve never attended a film festival, let me assure you it can often be a Cracker Jack surprise that can go either way. As I settled into enigmatic indie Head Like a Hole for Boston Underground Film Festival 2025 (BUFF 25), my first impressions were a little on the skeptical side, but those fears were alleviated quickly as its imaginative writing allows Head Like a Hole to subtly land jabs against bad workplaces everywhere. It’s a tremendous takedown of worker exploitation and business ethics, coming at a time when AI and other technologies threaten to diminish the labor class.
Opening in color briefly before heading strictly to black and white, I was afraid of what director Stefan MacDonald-Labelle had planned for his audience. As a critic, I’m no stranger to indie filmmaking techniques. Genre films often presented in black-and-white usually do so to cover something up. Production values and makeup effects are the main reasons. Still, I didn’t really understand why this movie, in particular, was venturing into the space of films like Laguna Ave, Divinity, Friend of the World, The Parker Sessions, and The Complex Forms when it seemed like strictly sanitized, psychological fare was expected.
Head Like a Hole introduces us to Asher (Steve Kasan) on what contends to rank highly on his list of the worst days of his life. Out of work, Asher runs out of gas while on his way to a job interview and has to hoof it fast to land a high-paying yet super mysterious job. Told to dress in a white shirt and tie, Asher arrives to find an idyllic-looking suburban household, where Emerson (Jeff McDonald) informs him of the task he’ll be managing in his new position. An eight-hour shift of staring at a fifteen-millimeter hole in the home’s foundation, taking measurements every hour to see if the size of the hole has been altered.
Though seemingly simple, minutes into the film, I was assessing the parts I was wary of. I’ve mentioned the black-and-white elements, but others were beginning to appear. At this point, it felt like we had met all the people in the film, and the movie was using a drawn-out exposition process. Emerson had slight intensity, but his compelling House of the Devil-styled dialogue, delivered urgently yet controlled, seemed to just keep going. Then, seeing the lackluster hole in the wall made me consider if MacDonald-Labelle would entertain us with ninety minutes of monotonous wall staring as his character’s brain melted from tedious boredom. After Emerson mentions that Asher should notate any auditory or visual oddities he experiences, hopes were higher as the co-writer-director was at least building confidence in the sandbox of hallucinatory sequences on the horizon. However, After getting to this point in Head Like a Hole, the movie pivots to an impressively entertaining Severance-like quality, aiming its subtext at soul-sucking, mind-numbing, life-consuming jobs.
Learning that Asher will be staying on-site for the duration of the project as a micromanaged researcher who isn’t privy to certain information that is unconducive to doing his job properly. The puzzling scenario gives big Cold Harbor project vibes from Apple TV+’s series, and as Asher stays at the work site, he experiences no separation between his personal and professional lives. As Asher starts discovering more about who is bankrolling the project, there are more Severance parallels in the spiritual hubris that exists to motivate employees at the job site. While not as densely layered as Severance’s configuration, Head Like a Hole constructs a very embroiled story that’s a bit more narrowly pointed, eventually propelling a climax that would leave Clive Barker impressed.
Writing duo Mitchell Brhelle and Stefan MacDonald-Labelle also touch upon concepts of overeager businesses fighting to ensure their and their employee’s destruction, all in the name of development. The film is filled with hypocritical praises and admonishments related to corporate culture policies and the initiatives that go against them. The near farcical satirization of a company owned by a righteous group cantankerously fighting against their beliefs is adeptly modern, and Macdonald-Labelle goes the extra step to show the frustrations Asher faces working for a place where he doesn’t fully understand what they’re doing. The company, wanting results, happily throws more money at Asher to pacify him, creating further moral dissonance but satisfying his earthly means. Head Like a Hole does a brilliant job of conflating the seven deadly sins into this journey to hell.
On the worker side of things, Head Like a Hole views workplace individualism with particular distinctions. The film sets Asher up with a mindset that suggests uniqueness isn’t warranted, but as Asher is encouraged to interact with the anomalous hole, the hole mysteriously begins to grow. Similar to the SXSW short film How Was Your Weekend?, Head Like a Hole’s individualist mechanics are undermined by the company’s internal posturing. As an office romance between Asher and his overnight counterpart Sam (Eric B. Hansen) begins to brew, corporate interference and beliefs affect their budding relationship. Yet, there is some disconnection in Emerson’s suggested therapeutic methods, asking Asher to reveal his authentic self to the hole to see if it helps the fifteen-millimeter hole grow. However, the established hypocrisy comes into play, making the premise feel more like a psychological social experiment.
As the film came to a close, I was far more enthralled by where Head Like a Hole ended its journey. It isn’t nearly what I initially anticipated, and that’s what is so wildly impressive about it. That subjective consternation I felt at the start had thoroughly dissipated by the climax, serving as a reminder to let films tell their stories and not judge them ahead of time. It may be a little bit of a slow roll for some, but the filmmakers undoubtedly give you something worth sticking around for. Films like Head Like a Hole have a way of changing my mind and getting me to get behind the story often wind up being the films I return to most. MacDonald-Labelle’s feature-length debut exemplifies true microbudget artistry and has the markings of becoming a midnight cult sensation. It’s a brazenly zeitgeisty affair worth checking out when it rolls into a film festival near you.
Head Like a Hole screens on Friday, March 21, as part of The Boston Underground Film Festival, which runs through Sunday. For tickets and additional information, please visit The Brattle Theatre’s website.
HEAD LIKE A HOLE | HORROR FEATURE FILM TEASER TRAILER
We’ve been gone a while, but it’s because we’ve been working on our first feature — Head Like a Hole! This is a pure DIY, lo-fi oddity for anyone who craves no-budget regional genre films. Catch us next at Boston Underground Film Festival, Salem Horror Fest & Panic Film Fest!
